meso-Zeaxanthin

meso-Zeaxanthin (3R,3´S-Zeaxanthin) is a xanthophyll carotenoid, as it contains oxygen and hydrocarbons, and is one of the three stereoisomers of zeaxanthin. Of the three stereoisomers, meso-zeaxanthin is the second most abundant in nature after 3R,3´R-zeaxanthin, which is produced by plants and algae. To date, meso-zeaxanthin has been identified in specific tissues of marine organisms and in the macula lutea, also known as the "yellow spot", of the human retina.

meso-Zeaxanthin
Names
IUPAC name
(3R,3′S)-β,β-Carotene-3,3′-diol
Systematic IUPAC name
(1R)-4-{(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(4S)-4-Hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl}-3,5,5-trimethylcyclohex-3-en-1-ol
Other names
3R,3'S zeaxanthin
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • InChI=1S/C40H56O2/c1-29(17-13-19-31(3)21-23-37-33(5)25-35(41)27-39(37,7)8)15-11-12-16-30(2)18-14-20-32(4)22-24-38-34(6)26-36(42)28-40(38,9)10/h11-24,35-36,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t35-,36+
    Key: JKQXZKUSFCKOGQ-YOPUJPICSA-N
  • CC1=C(C(C[C@@H](C1)O)(C)C)/C=C/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C=C/C2=C(C[C@@H](CC2(C)C)O)C)\C)\C)/C)/C
Properties
C40H56O2
Molar mass 568.87144 g/mol
Appearance orange-red
insol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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